{(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane

Base Information

• Chemical Name: {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane
• CAS No.: 667421-76-3
• Molecular Formula: C₂₈H₃₆O₄SSi
• Molecular Weight: 496.743

Synonyms:{(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane

Chemical Property of {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane

There total 28 articles about {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.03,7]dodec-4-yl]ethan-1-ol (667421-98-9) → {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.01,12.03,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane (667421-76-3)

Guidance literature:

With ytterbium(III) triflate; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tetlet.2003.10.161

Reference yield:

methyl (2E)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-hydroxyoxolan-2-yl]prop-2-enoate (667421-80-9) → {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.01,12.03,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane (667421-76-3)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C

3.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

4.1: PivCl; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

4.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

5.1: LHMDS / tetrahydrofuran / 0.75 h / -78 °C

5.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

6.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

7.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂

8.1: LMHDS / tetrahydrofuran / 1 h / -78 °C

8.2: 0.93 g / -78 °C

9.1: 95 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 20 °C

10.1: 61 percent / MS₄Angstroem; DDQ / CH₂Cl₂ / 0.25 h / 20 °C

11.1: 91 percent / iPr₂NEt / CH₂Cl₂ / 40 h / Heating

12.1: 91 percent / aq. AcOH / 1 h / 20 °C

13.1: 88 percent / pyridine / CH₂Cl₂ / 6 h / 20 °C

14.1: 77 percent / hydrogen; Pd(OH)2-C / ethyl acetate / 13 h / 20 °C

15.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

16.1: 79 percent / Na₂S*9H₂O / dimethylformamide / 0.08 h / 100 °C

17.1: 83 percent / ZnBr₂ / CH₂Cl₂ / 8 h / 20 °C

18.1: 89 percent / SO₃*Py; i-Pr₂NEt / dimethylsulfoxide; CH₂Cl₂ / 0.33 h / 20 °C

19.1: 86 percent / CSA / methanol / 3 h / 20 °C

20.1: DMAP / CH₂Cl₂ / 18 h / 20 °C

21.1: 84.2 mg / DIBAL-H / toluene / 0.17 h / -78 °C

22.1: 97 percent / Yb(OTf)3 / acetonitrile / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium sulfide; lithium hydroxide; AD-mix-α; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; methanesulfonamide; palladium hydroxide - carbon; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; pivaloyl chloride; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; lithium hexamethyldisilazane; ytterbium(III) triflate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 8.2: Julia olefination / 9.1: Sharpless asymmetric dihydroxylation;

DOI:10.3987/com-03-9952

Reference yield:

methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate (667421-81-0) → {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.01,12.03,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane (667421-76-3)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

2.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C

4.1: 8.82 g / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 2 h / 20 °C

5.1: PivCl; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

5.2: 88 percent / LiCl / tetrahydrofuran / 2 h / 20 °C

6.1: LHMDS / tetrahydrofuran / 0.75 h / -78 °C

6.2: 78 percent / LiI / tetrahydrofuran / 1 h / -50 °C

7.1: 91 percent / LiBH₄ / ethanol; tetrahydrofuran; H₂O / 2 h / 0 °C

8.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂

9.1: LMHDS / tetrahydrofuran / 1 h / -78 °C

9.2: 0.93 g / -78 °C

10.1: 95 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 20 °C

11.1: 61 percent / MS₄Angstroem; DDQ / CH₂Cl₂ / 0.25 h / 20 °C

12.1: 91 percent / iPr₂NEt / CH₂Cl₂ / 40 h / Heating

13.1: 91 percent / aq. AcOH / 1 h / 20 °C

14.1: 88 percent / pyridine / CH₂Cl₂ / 6 h / 20 °C

15.1: 77 percent / hydrogen; Pd(OH)2-C / ethyl acetate / 13 h / 20 °C

16.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

17.1: 79 percent / Na₂S*9H₂O / dimethylformamide / 0.08 h / 100 °C

18.1: 83 percent / ZnBr₂ / CH₂Cl₂ / 8 h / 20 °C

19.1: 89 percent / SO₃*Py; i-Pr₂NEt / dimethylsulfoxide; CH₂Cl₂ / 0.33 h / 20 °C

20.1: 86 percent / CSA / methanol / 3 h / 20 °C

21.1: DMAP / CH₂Cl₂ / 18 h / 20 °C

22.1: 84.2 mg / DIBAL-H / toluene / 0.17 h / -78 °C

23.1: 97 percent / Yb(OTf)3 / acetonitrile / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium sulfide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; AD-mix-α; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; methanesulfonamide; palladium hydroxide - carbon; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; pivaloyl chloride; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; lithium hexamethyldisilazane; ytterbium(III) triflate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 9.2: Julia olefination / 10.1: Sharpless asymmetric dihydroxylation;

DOI:10.3987/com-03-9952

upstream raw materials:

2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethan-1-ol

tert-butylchlorodiphenylsilane

2-[(1R,3S,4R,7R,9R,11S)-11-hydroxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethyl 2,2-dimethylpropanoate

methyl (2E)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-hydroxyoxolan-2-yl]prop-2-enoate

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